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Search results; Over 1,000 homes in Madison

Top guest favourite

Farm stay in Madison

Madison Nature Getaway

1 bedroom, 2 beds, 1 private bathroom

25–30 Aug

$850 SGD for 5 nights

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4.98 out of 5 average rating, 225 reviews

Guest favourite

Home in Woolford

"Endless Summer" on the Chesapeake!

4 bedrooms, 7 beds, 2.5 bathrooms

17–22 Aug

$6,429 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 5 reviews

Guest favourite

Home in Woolford

Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba

7 bedrooms, 13 beds, 5 bathrooms

29 Aug – 3 Sept

$9,815 SGD for 5 nights

4.98 out of 5 average rating, 87 reviews

Guest favourite

Place to stay in Cambridge

Wye Three Oaks

2 bedrooms, 4 beds, 1 bathroom

2–7 Aug

$1,491 SGD for 5 nights

Pay $0 today

Free cancellation

4.96 out of 5 average rating, 99 reviews

Top guest favourite

Home in Madison

Madison Bay Club House

3 bedrooms, 7 beds, 2.5 bathrooms

27 Aug – 1 Sept

$2,532 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 50 reviews

Top guest favourite

Home in Woolford

Starboard on McKeil Point, w/heated pool & hot tub

6 bedrooms, 11 beds, 4.5 bathrooms

5–10 Sept

$9,228 SGD for 5 nights

4.99 out of 5 average rating, 142 reviews

Top guest favourite

Home in Woolford

Waterfront Getaway with Dock

3 bedrooms, 4 beds, 2 bathrooms

23–28 Aug

$1,674 SGD for 5 nights

Pay $0 today

Free cancellation

4.94 out of 5 average rating, 188 reviews

Top guest favourite

Home in Cambridge

Sunset Breezes - quiet waterfront retreat

3 bedrooms, 5 beds, 2 bathrooms

23–28 Aug

$3,227 SGD for 5 nights

Pay $0 today

Free cancellation

4.99 out of 5 average rating, 219 reviews

Top guest favourite

Home in Cambridge

Relaxing Retreat on the Hudson

5 bedrooms, 5 beds, 2 bathrooms

24–29 Aug

$2,018 SGD for 5 nights

4.96 out of 5 average rating, 74 reviews

Top guest favourite

Home in Woolford

Newly Renovated Modern 3 bed 2 bath Water Front

3 bedrooms, 3 beds, 2 bathrooms

11–16 Aug

$2,651 SGD for 5 nights

5.0 out of 5 average rating, 247 reviews

Superhost

Home in Woolford

Eastern Shore Waterfront-Pier, Kayaks, FirePit

2 bedrooms, 4 beds, 1 bathroom

14–19 Aug

$2,817 SGD for 5 nights

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Free cancellation

Superhost

Home in Woolford

The Blue Heron-Spacious Waterfront house w/ kayaks

6 bedrooms, 10 beds, 4 bathrooms

16–21 Aug

$3,421 SGD for 5 nights

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Free cancellation

4.67 out of 5 average rating, 58 reviews

Guest favourite

Home in Cambridge

Chesapeake Sunset Retreat

4 bedrooms, 5 beds, 1.5 bathrooms

8–13 Sept

$2,577 SGD for 5 nights

Pay $0 today

Free cancellation

4.83 out of 5 average rating, 35 reviews

Home in Cambridge

Family and Pet-Friendly, Waterfront with Pier

4 bedrooms, 5 beds, 1.5 bathrooms

27 Sept – 2 Oct

$2,283 SGD for 5 nights

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Free cancellation

Guest favourite

Home in Cambridge

Choptank Riverside Retreat

3 bedrooms, 4 beds, 2 bathrooms

3–8 Aug

$3,226 SGD for 5 nights

4.92 out of 5 average rating, 12 reviews

Holiday home in Cambridge

Very Private and Spacious Waterfront Family House

8 bedrooms, 15 beds, 6.5 bathrooms

15–22 Aug

$10,146 SGD for 7 nights

4.76 out of 5 average rating, 68 reviews

Top guest favourite

Home in Madison

Bayfront Gem w/ Amazing Water Views + Pond!

4 bedrooms, 7 beds, 2.5 bathrooms

30 Aug – 4 Sept

$3,040 SGD for 5 nights

4.97 out of 5 average rating, 59 reviews

Superhost

Home in Church Creek

Blackwater River Lodge

8 bedrooms, 9 beds, 4 bathrooms

8–13 Aug

$4,146 SGD for 5 nights

Pay $0 today

Free cancellation

4.77 out of 5 average rating, 13 reviews

Guest favourite

Home in Cambridge

Modern Chesapeake Waterfront - Heated Pool - Dock

5 bedrooms, 8 beds, 3.5 bathrooms

20–25 Sept

$5,158 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews